Dimethylformamide → 3-Bromobenzaldehyde

Temperature

0 °C

n-Butylmagnesium chloride (4.00 mmol) in 2.00M tetrahydrofuran solution (2.00 mL) was added to ice-cooled n-butyllithium (8.06 mmol) in 1.55M hexane (5.20 mL). The mixture was stirred at 0° C. for 15 minutes to give a suspension. To the suspension was added dropwise a toluene solution (25 mL) containing 1,3-dibromobenzene (2.36 g, 10.0 mmol), while keeping the temperature below 5° C., over a period of 15 minutes, thereby to give a suspension. The suspension was stirred at 0° C. for 5 hours, and then N,N-dimethylformamide (1.0 mL, 13 mmol) was added thereto. The resultant mixture was stirred at 0° C. for 30 minutes, and 10% aqueous acetic acid (20 mL) was added. The reaction mixture was extracted twice with toluene (20 mL). The organic extracts were combined, washed with water (20 mL), and dried over magnesium sulfate. Toluene was added to the solution to a volume of 85 mL. The solution (83 ml) was purified by flash column chromatography on silica gel in a developing solvent system of hexane-ethyl acetate (25:1, v/v) to give the title compound (1.446 g, 78% yield) as a pale yellowish crystalline solid.

1. customto give a suspension
2. customthe temperature below 5° C.
3. waitover a period of 15 minutes
4. customto give a suspension
5. stirringThe suspension was stirred at 0° C. for 5 hours
6. extractionThe reaction mixture was extracted twice with toluene (20 mL)
7. washwashed with water (20 mL)
8. dry with materialdried over magnesium sulfate
9. additionToluene was added to the solution to a volume of 85 mL
10. customThe solution (83 ml) was purified by flash column chromatography on silica gel in a developing solvent system of hexane-ethyl acetate (25:1

ORD record

ord-b61760b05124402bb894b98c8d0f50df

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439535B2